Aniline → N-(2-Methylbut-3-yn-2-yl)aniline

Temperature

15 °C

A mixture of aniline (21.8 g, 234 mmol) and triethylamine (26.6 g, 263.3 mmol) in 100 mL ether, 25 mL water, 0.2 g copper (I) chloride and 0.2 g copper bronze was prepared under nitrogen in a three-neck flask equipped with mechanical stirrer. 3-Chloro-3-methyl-1-butyne (20 g, 195 mmol) in ether (25 mL) was slowly added with stirring while maintaining an inside temperature at 10-20° C. After stirring for an additional 2 hours at room temperature, the mixture was poured into a mixture of 200 mL ether and 100 mL water. The ethereal layer was washed with cold water, dried for 15 minutes over anhydrous potassium carbonate and filtered, redried with potassium hydroxide pellets overnight. The solution was filtered and concentrated under reduced pressure.

1. customwas prepared under nitrogen in a three-neck flask
2. customequipped with mechanical stirrer
3. stirringAfter stirring for an additional 2 hours at room temperature
4. washThe ethereal layer was washed with cold water
5. dry with materialdried for 15 minutes over anhydrous potassium carbonate
6. filtrationfiltered
7. dry with materialredried with potassium hydroxide pellets overnight
8. filtrationThe solution was filtered
9. concentrationconcentrated under reduced pressure

ORD record

ord-2e0c446124d3411691f3e63db5de0710

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867198B2